Abstract
Isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles (Cu-IS-AMBA-MNPs) as a new catalyst was designed, prepared and characterized by appropriate analyses. The heterogeneous reusable catalyst was successfully used for the efficient and widespread syntheses of diaryl ethers and diarylamines via the Ullmann coupling reaction. This green catalyst was easily removed, reused several times with no significant loss of its activity, and provided a clean synthesis with excellent yield and reduced time.
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References
J.S. Sawyer, Tetrahedron 56, 5045 (2000)
X. Zhang, F. Liu, Z. Wei, Z.O. Wang, Lett. Org. Chem. 10, 31 (2013)
H.J. Cristau, P.P. Cellier, S. Hamada, J.F. Spindler, M. Taillefer, Org. Lett. 6, 913 (2004)
K.C. Nicolaou, C.N.C. Boddy, S. Brase, N. Winssinger, Angew. Chem. Int. Ed. 38, 2096 (1999)
K.C. Nicolaou, S. Natarajan, H. Li, N.F. Jain, R. Huges, M.E. Solomon, J.M. Ramanujulu, C.N.C. Boddy, M. Takayanagi, Angew. Chem. Int. Ed. 37, 2708 (1998)
Q. Zhang, D.P. Wang, X.Y. Wang, K. Ding, J. Org. Chem. 74, 7187 (2009)
F. Ullmann, Chem. Ber. Dtsch. Chem. Ges. 37, 853 (1904)
A. Shaabani, S.E. Afshari, R. Hooshmand, A.T. Tabatabaei, F. Hajishaabanha, RSC Adv. 6, 18113 (2016)
J. Lindley, Tetrahedron 40, 1433 (1984)
J.C. Henrim, P.C. Pascal, H. Samy, F.S. Jean, Org. Lett. 6, 913 (2004)
Y. Zhang, G. Ni, C. Li, S. Xu, Z. Zhang, X. Xie, Tetrahedron 71, 4927 (2015)
S. Handa, Y. Wang, F. Gallou, B.H. Lipshutz, Science 349, 1087 (2015)
J.Y. Kim, J.C. Park, A. Kim, A.Y. Kim, H.J. Lee, H. Song, K.H. Park, Eur. J. Inorg. Chem. 28, 4219 (2009)
K. Huang, Y. Chen, J.H. Chan, L.R. Mike, D.L. Robert, Synlett 10, 1419 (2011)
V.R. Choudhary, D.K. Dumbre, P.N. Yadav, S.K. Bhargava, Catal. Commun. 29, 132 (2011)
S.A.R. Mulla, S.M. Inamdar, M.Y. Pathan, S.S. Chavan, Tetrahedron Lett. 53, 1826 (2012)
F. Zhou, J. Guo, J. Liu, K. Ding, S. Yu, Q. Cai, J. Am. Chem. Soc. 134, 14326 (2012)
S.G. Babu, R. Karvembu, Tetrahedron Lett. 54, 1677 (2013)
R.K. Gujadhur, C.G. Bates, D. Venkataraman, Org. Lett. 3, 4315 (2001)
F.Y. Kwong, A. Klapars, S.L. Buchwald, Org. Lett. 4, 581 (2002)
H.J. Cristau, P.P. Cellier, J.F. Spindler, M. Taillefer, Org. Lett. 6, 913 (2004)
S. Zhang, D. Zhang, L.S. Liebeskind, J. Org. Chem. 62, 2312 (1997)
A.A. Kelkar, N.M. Patil, R.V. Chaudhari, Tetrahedron Lett. 43, 7143 (2002)
A.S. Gajare, K. Toyota, M. Yoshifuji, F. Yoshifuji, Chem. Commun. 17, 1994 (2004)
E. Buck, Z.J. Song, D. Tschaen, P.G. Dormer, R.P. Volante, P.J. Reider, Org. Lett. 4, 1623 (2002)
C. Palomo, M. Oiarbide, R. Lopez, E. Gomez-Bengoa, Chem. Commun. 19, 2091 (1998)
D. Ma, Q. Cai, Org. Lett. 5, 3799 (2003)
N.K. Ojha, G.V. Zyryanov, A. Majee, V.N. Charushin, O.N. Chupakhin, S. Santra, Coord. Chem. Rev. 353, 1 (2017)
J.S. Zheng, X.S. Zhang, P. Li, J. Zhu, X.G. Zhou, W.K. Yuan, Electrochem. Commun. 9, 895 (2007)
W. Wu, Q. He, C. Jiang, Nanoscale Res. Lett. 3, 397 (2008)
A. Wang, X. Liu, Z. Su, H. Jing, Catal. Sci. Tech. 4, 71 (2014)
S. Fan, W. Dong, X. Huang, H. Gao, J. Wang, Z. Jin, J. Tang, G. Wang, ACS Catal. 7, 243 (2016)
K. Mishra, T.N. Poudel, N. Basavegowda, Y.R. Lee, J. Catal. 344, 273 (2016)
H.N. Dadhania, K.R. Dipak, N.D. Abhishek, Catal. Sci. Tech. 5, 4806 (2015)
X. An, D. Cheng, L. Dai, B. Wang, H.J. Ocampo, J. Nasrallah, X. Jia, J. Zou, Y. Long, Y. Ni, Appl. Catal. B 206, 53 (2017)
M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Rostami, A. Zare, N. Iranpoor, R. Luque, Green Chem. 15, 2132 (2013)
M. M. Khodaei, A. Alizadeh, M. Haghipour, Res. Chem. Inter. (2017). https://doi.org/10.1007/s11164-017-3008-2
K. He, Y. Ma, B. Yang, C. Liang, X. Chen, C. Cai, Mol. Biomol. Spectrosc. 173, 82 (2017)
S. Liu, H. Wang, L. Chai, M. Li, J. Coll. Inter. Sci. 478, 288 (2016)
R. Mirzajani, S. Ahmadi, J. Ind. Eng. Chem. 23, 171 (2015)
M.A. Rahman, U. Culsum, A. Kumar, H. Gao, N. Hu, Int. J. Biol. Macromolec. 87, 488 (2016)
D. Yang, J. Hu, S. Fu, J. Phys. Chem. C 113, 7646 (2009)
R. Singh, B.K. Allam, D.S. Raghuvanshi, K.N. Singh, Tetrahedron 69, 1038 (2013)
J.C. Vantourout, R.P. Law, A. Isidro-Llobet, S.J. Atkinson, A.J. Watson, J. Org. Chem. 81, 3942 (2016)
A. Ghorbani-Choghamarani, Z. Taherinia, Z. New J. Chem. 41, 9414 (2017)
L. Cai, X. Qian, W. Song, T. Liu, X. Tao, W. Li, X. Xie, Tetrahedron 70, 4754 (2014)
J. Liu, D. Yang, X. Yang, M. Nie, G. Wu, Z. Wang, P. Gong, Bio. Med. Chem. 25, 4475 (2017)
K. Kulangiappar, M. Anbukulandainathan, T. Raju, Synth. Commun. 1, 2494 (2014)
S. Yamada, M. Ishikawa, C. Kaneko, Chem. Pharm. Bull. 23, 2818 (1975)
A. Kumar, B.S. Bhakuni, C.D. Prasad, S. Kumar, S. Kumar, Tetrahedron 69, 5383 (2013)
H. Xu, Y. Chen, Synth. Commun. 37, 2411 (2007)
F. Damkaci, C. Sigindere, T. Sobiech, E. Vik, J. Malone, Tetrahedron Lett. 58, 3559 (2017)
M. Khalilzadeh, A. Hosseini, A. Pilevar, Eur. J. Org. Chem. 8, 1587 (2011)
R. Arundhathi, D. Damodara, P.R. Likhar, M.L. Kantam, P. Saravanan, T. Magdaleno, S.H. Kwon, Adv. Syn. Catal. 353, 1591 (2011)
S. Verma, N. Kumar, S.L. Jain, Tetrahedron Lett. 53, 4665 (2012)
X. Liu, S. Zhang, Synlett 2, 268 (2011)
B. Kaboudin, Y. Abedi, T. Yokomatsu, Eur. J. Org. Chem. 33, 6656 (2011)
J.C. Antilla, S.L. Buchwald, Org. Lett. 3, 2077 (2001)
M.L. Kantam, G.T. Venkanna, C. Sridhar, B. Sreedhar, B.M. Choudary, J. Org. Chem. 71, 9522 (2006)
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We thank the Research Council of Razi University for generous financial support of this work.
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Khodaei, M.M., Alizadeh, A. & Haghipour, M. Preparation and characterization of isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles as a novel magnetic catalyst for the Ullmann coupling reaction. Res Chem Intermed 45, 2727–2747 (2019). https://doi.org/10.1007/s11164-019-03760-0
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DOI: https://doi.org/10.1007/s11164-019-03760-0